Abstract
The reaction of the benzyl Grignard reagent with alkyl chloroformates has been investigated. The reaction with methyl chloroformate afforded methyl phenylacetate 1, methyl o-toluate C 2j and, in addition, a trace of dimethyl homophthalate C 3. The formation of C 2D decreased with increasing basicity of the solvents in the order: Et20 THF THF-1-HMPA. The diminished yield of C2D was obtained also in the reaction of benzyllithium which has higher ionic character of the C-M bonds relative to the Grignard reagent. The formation of o-toluate C2 decreased in the order of the reactivity of alkyl chloroformates; C1COOCH3 C1COOC2H5, C1COO(CH2)3CH81COOCH2CH(CF18)2 C1C00(Cli2)8CH3. A plausible reaction pathway is proposed on the basis of these findings.
